EP1562596A1 - Derives de pyridinalkyl-aminoalkyl-1h-indole inhibant les recepteurs 5-ht et la recapture de la serotonine, pouvant servir d'antidepresseurs et d'anxiolytiques - Google Patents
Derives de pyridinalkyl-aminoalkyl-1h-indole inhibant les recepteurs 5-ht et la recapture de la serotonine, pouvant servir d'antidepresseurs et d'anxiolytiquesInfo
- Publication number
- EP1562596A1 EP1562596A1 EP03811744A EP03811744A EP1562596A1 EP 1562596 A1 EP1562596 A1 EP 1562596A1 EP 03811744 A EP03811744 A EP 03811744A EP 03811744 A EP03811744 A EP 03811744A EP 1562596 A1 EP1562596 A1 EP 1562596A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- indole
- butyl
- carbonitrile
- amino
- ylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 229940076279 serotonin Drugs 0.000 title claims abstract description 11
- 230000000949 anxiolytic effect Effects 0.000 title claims abstract description 8
- 239000000935 antidepressant agent Substances 0.000 title claims abstract description 7
- 229940005513 antidepressants Drugs 0.000 title claims abstract description 7
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- 230000002401 inhibitory effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- -1 COOA Chemical group 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 50
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
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- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
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- REWFCFCTENNIAM-UHFFFAOYSA-N 3-[4-(pyridin-2-ylmethylamino)butyl]-1h-indole-5-carbonitrile Chemical compound C12=CC(C#N)=CC=C2NC=C1CCCCNCC1=CC=CC=N1 REWFCFCTENNIAM-UHFFFAOYSA-N 0.000 claims description 2
- BGRIIAVSULCHQF-UHFFFAOYSA-N 3-[4-(quinolin-2-ylmethylamino)butyl]-1h-indole-5-carbonitrile Chemical compound C1=CC=CC2=NC(CNCCCCC3=CNC4=CC=C(C=C43)C#N)=CC=C21 BGRIIAVSULCHQF-UHFFFAOYSA-N 0.000 claims description 2
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- HRLXIYDYCSMIGS-UHFFFAOYSA-N 3-[4-[(2,6-dichloropyridin-3-yl)methylamino]butyl]-1h-indole-5-carbonitrile Chemical compound ClC1=NC(Cl)=CC=C1CNCCCCC1=CNC2=CC=C(C#N)C=C12 HRLXIYDYCSMIGS-UHFFFAOYSA-N 0.000 claims description 2
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- YLXDNBFSQCUOHH-UHFFFAOYSA-N 3-[4-[(5-methylpyridin-3-yl)methylamino]butyl]-1h-indole-5-carbonitrile Chemical compound CC1=CN=CC(CNCCCCC=2C3=CC(=CC=C3NC=2)C#N)=C1 YLXDNBFSQCUOHH-UHFFFAOYSA-N 0.000 claims description 2
- AXNACVKITYMSDB-UHFFFAOYSA-N 3-[4-[(5-phenylpyridin-2-yl)methylamino]butyl]-1h-indole-5-carbonitrile Chemical compound C12=CC(C#N)=CC=C2NC=C1CCCCNCC(N=C1)=CC=C1C1=CC=CC=C1 AXNACVKITYMSDB-UHFFFAOYSA-N 0.000 claims description 2
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- JSKIZQHKCXVWMU-UHFFFAOYSA-N 3-[4-[[2-(4-chlorophenoxy)pyridin-3-yl]methylamino]butyl]-1h-indole-5-carbonitrile Chemical compound C1=CC(Cl)=CC=C1OC1=NC=CC=C1CNCCCCC1=CNC2=CC=C(C#N)C=C12 JSKIZQHKCXVWMU-UHFFFAOYSA-N 0.000 claims description 2
- JBDCCAMFPIDMMN-UHFFFAOYSA-N 3-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]butyl]-1h-indole-5-carbonitrile Chemical compound C1=NC(C(F)(F)F)=CC=C1CNCCCCC1=CNC2=CC=C(C#N)C=C12 JBDCCAMFPIDMMN-UHFFFAOYSA-N 0.000 claims description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- RYGIHSLRMNXWCN-UHFFFAOYSA-N quinoline-3-carbaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CN=C21 RYGIHSLRMNXWCN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960001879 ropinirole Drugs 0.000 description 1
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
- 229960004603 tolcapone Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Definitions
- the 5-HT- D affinity can be determined, for example, by the method described by Pauwels and Palmier in Neuropharmacology, 33, 67 (1994).
- the compounds according to the invention are also particularly suitable for the treatment of neurodegenerative diseases, such as, for example, lathyrism, Alzheimer's, Parkinson's and Huntington's.
- the compounds of formula I are particularly suitable for the treatment of side effects which occur in the treatment of idiopathic Parkinson's disease with conventional Parkinson's medication. Therefore, they can also be used as add-on therapy in the treatment of Parkinson's disease.
- Active ingredient is the logD value, because this value is a measure of the lipophilicity of a molecule.
- the invention relates to the compounds of formula I and their salts and solvates according to claim 1 and a process for the preparation of compounds of formula I and their salts and solvates, characterized in that
- a ' preferably denotes alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, trifluoromethyl or benzyl.
- Ar means e.g. unsubstituted phenyl, naphthyl or biphenyl, further preferably e.g. by A, fluorine, chlorine, bromine, iodine, hydroxy, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, nitro, cyan, formyl, acetyl,
- compounds of formula I with bases can be converted into the corresponding metal, in particular alkali metal or alkaline earth metal or into the corresponding ammonium salts.
- the invention also relates to the compounds of the formula I as claimed in claim 1 and their physiologically acceptable salts or solvates for use in combating diseases.
- Compounds of the formula I according to the invention can be chiral due to their molecular structure and can accordingly occur in various enantiomeric forms. They can therefore be in racemic or optically active form.
- a mixture of 20 g of an active ingredient of the formula I is melted with 100 g of soy lecithin and 1400 g of cocoa butter, poured into molds and allowed to cool. Each suppository contains 20 mg of active ingredient.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
L'invention concerne des nouveaux dérivés d'indole de formule (I) dans laquelle X, Y, R<1>, R<1'>, m et n sont tels que définis dans la première revendication. Ces composés présentent une forte affinité envers les récepteurs 5-HT1A et une affinité partielle envers les récepteurs 5-HT1D. Lesdits composés inhibent la recapture de la sérotonine, présentent des propriétés agonistes et antagonistes envers la sérotonine et peuvent être utilisés en tant qu'antidépresseurs et anxiolytiques ainsi que pour traiter des maladies neurodégénératives.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10254596A DE10254596A1 (de) | 2002-11-22 | 2002-11-22 | Indolderivate |
| DE10254596 | 2002-11-22 | ||
| PCT/EP2003/012081 WO2004047840A1 (fr) | 2002-11-22 | 2003-10-30 | Derives de pyridinalkyl-aminoalkyl-1h-indole inhibant les recepteurs 5-ht et la recapture de la serotonine, pouvant servir d'antidepresseurs et d'anxiolytiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1562596A1 true EP1562596A1 (fr) | 2005-08-17 |
| EP1562596B1 EP1562596B1 (fr) | 2006-08-30 |
Family
ID=32240308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03811744A Expired - Lifetime EP1562596B1 (fr) | 2002-11-22 | 2003-10-30 | Derives de pyridinalkyl-aminoalkyl-1h-indole inhibant les recepteurs 5-ht et la recapture de la serotonine, pouvant servir d'antidepresseurs et d'anxiolytiques |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7432282B2 (fr) |
| EP (1) | EP1562596B1 (fr) |
| JP (1) | JP4523416B2 (fr) |
| KR (1) | KR20050085038A (fr) |
| CN (1) | CN1708303A (fr) |
| AT (1) | ATE337781T1 (fr) |
| AU (1) | AU2003302361B2 (fr) |
| BR (1) | BR0316721A (fr) |
| CA (1) | CA2506960C (fr) |
| DE (2) | DE10254596A1 (fr) |
| ES (1) | ES2271697T3 (fr) |
| MX (1) | MXPA05005278A (fr) |
| PL (1) | PL375259A1 (fr) |
| WO (1) | WO2004047840A1 (fr) |
| ZA (1) | ZA200505037B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7994331B2 (en) * | 2005-07-13 | 2011-08-09 | Msd K.K. | Heterocycle-substituted benzimidazole derivative |
| WO2007148341A2 (fr) | 2006-06-22 | 2007-12-27 | Ramot At Tel Aviv University Ltd. | Nouveaux inhibiteurs de la recapture de la sérotonine en tant que médicaments ayant une activité se limitant au système périphérique |
| US9278947B2 (en) | 2006-06-22 | 2016-03-08 | Ramot At Tel-Aviv University Ltd. | Serotonin reuptake inhibitors as drugs having peripheral-system-restricted activity |
| WO2015090235A1 (fr) * | 2013-12-20 | 2015-06-25 | Sunshine Lake Pharma Co., Ltd. | Composés pipéraziniques substitués et leurs procédés d'utilisation |
| US10316025B2 (en) | 2015-06-03 | 2019-06-11 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
| HRP20220331T1 (hr) | 2018-03-08 | 2022-05-13 | Incyte Corporation | Spojevi aminopirazin diola kao inhibitori pi3k-y |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| WO2020183011A1 (fr) | 2019-03-14 | 2020-09-17 | Institut Curie | Inhibiteurs de htr1d et leurs utilisations dans le traitement du cancer |
| CN111689944B (zh) * | 2020-06-10 | 2021-11-16 | 中山大学 | 喹啉色胺杂联体及其在制备治疗阿尔茨海默病的药物中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4748182A (en) * | 1986-03-05 | 1988-05-31 | Merrell Dow Pharmaceuticals Inc. | Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)one-1,1-dioxide derivatives and their use as anti-hypertensive and anxiolytic agents |
| FR2614022B1 (fr) * | 1987-04-15 | 1989-12-01 | Roussel Uclaf | Nouveaux derives 17-aza de 20,21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et ces compositions les renfermant |
| DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| WO1996020191A1 (fr) | 1994-12-28 | 1996-07-04 | Sankyo Company, Limited | Derives d'indole |
| US5942536A (en) * | 1995-10-10 | 1999-08-24 | Eli Lilly And Company | N- 2-substituted-3-(2-aminoethyl)-1H-indol-5-YL!-Amides: new 5-HT1F agonists |
| CA2207137A1 (fr) * | 1996-06-14 | 1997-12-14 | James Erwin Fritz | Procede combinatoire a l'aide d'agent d'elimination pour la preparation de banques d'amine secondaire |
| DE10029371A1 (de) | 2000-06-20 | 2002-01-03 | Merck Patent Gmbh | Heterocyclische Aminoalkylpyridinderivate als Psychopharmaka |
-
2002
- 2002-11-22 DE DE10254596A patent/DE10254596A1/de not_active Withdrawn
-
2003
- 2003-10-30 MX MXPA05005278A patent/MXPA05005278A/es unknown
- 2003-10-30 BR BR0316721-6A patent/BR0316721A/pt not_active Application Discontinuation
- 2003-10-30 PL PL03375259A patent/PL375259A1/xx not_active Application Discontinuation
- 2003-10-30 ES ES03811744T patent/ES2271697T3/es not_active Expired - Lifetime
- 2003-10-30 JP JP2004554301A patent/JP4523416B2/ja not_active Expired - Fee Related
- 2003-10-30 KR KR1020057008921A patent/KR20050085038A/ko not_active Application Discontinuation
- 2003-10-30 CA CA2506960A patent/CA2506960C/fr not_active Expired - Fee Related
- 2003-10-30 CN CNA2003801023956A patent/CN1708303A/zh active Pending
- 2003-10-30 US US10/535,916 patent/US7432282B2/en not_active Expired - Fee Related
- 2003-10-30 DE DE50304892T patent/DE50304892D1/de not_active Expired - Lifetime
- 2003-10-30 EP EP03811744A patent/EP1562596B1/fr not_active Expired - Lifetime
- 2003-10-30 AT AT03811744T patent/ATE337781T1/de not_active IP Right Cessation
- 2003-10-30 WO PCT/EP2003/012081 patent/WO2004047840A1/fr active IP Right Grant
- 2003-10-30 AU AU2003302361A patent/AU2003302361B2/en not_active Ceased
-
2005
- 2005-06-21 ZA ZA200505037A patent/ZA200505037B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2004047840A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006508991A (ja) | 2006-03-16 |
| PL375259A1 (en) | 2005-11-28 |
| MXPA05005278A (es) | 2005-07-25 |
| JP4523416B2 (ja) | 2010-08-11 |
| US7432282B2 (en) | 2008-10-07 |
| WO2004047840A1 (fr) | 2004-06-10 |
| ATE337781T1 (de) | 2006-09-15 |
| BR0316721A (pt) | 2005-10-18 |
| AU2003302361B2 (en) | 2009-06-18 |
| EP1562596B1 (fr) | 2006-08-30 |
| AU2003302361A1 (en) | 2004-06-18 |
| ES2271697T3 (es) | 2007-04-16 |
| DE10254596A1 (de) | 2004-06-03 |
| CN1708303A (zh) | 2005-12-14 |
| ZA200505037B (en) | 2006-11-29 |
| CA2506960A1 (fr) | 2004-06-10 |
| DE50304892D1 (de) | 2006-10-12 |
| KR20050085038A (ko) | 2005-08-29 |
| CA2506960C (fr) | 2012-04-10 |
| US20060063811A1 (en) | 2006-03-23 |
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